


The Classics

by angstriddenwriter



Category: Supernatural
Genre: Angst, Classic Cars, F/M, Smut
Language: English
Status: In-Progress
Published: 2021-02-20
Updated: 2021-02-20
Packaged: 2021-03-16 13:42:26
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 2
Words: 2,506
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29576985
Author URL: https://archiveofourown.org/users/angstriddenwriter/pseuds/angstriddenwriter
Summary: This series will be a Demon!Dean x Reader angst-fest based on some of my favorite Classic Rock songs. Each chapter will be named after and inspired by a song. I’ll make a coordinating playlist and add the link to each chapter. This chapter list is what I’ve currently got planned, but it might possibly get a bit longer depending on how things pan out. (Smut is marked with an asterisk)Paint It BlackThe JokerFat Bottomed Girls*Dirty Deeds (Done Dirt Cheap)(I Can’t Get No) Satisfaction*RenegadeFortunate SonLaylaI Want You To Want MeHello, I Love YouCrazy On You*
Relationships: Dean Winchester/Reader, Demon Dean/Reader, Mark of Cain Dean/Reader





	1. Paint It Black

Great. Just great. Your baby would break down on a hot day like this while you were just a couple miles out from your destination. You threw the hood up in a huff, still being more delicate than most would. It is your baby after all. This truck had become your life and your escape. When shit hit the fan, you fiddled with the fan belt. It probably wasn’t the best coping mechanism, but it was the most rewarding to you. 

You tinkered around a bit before discovering the problem- a broken spark plug. It’d be a quick and easy fix, but you didn’t have any spares in your toolkit. You silently cursed yourself, you knew you should have bought a pack the other day. 

“It’s pretty, but it’d look a lot better if it were black.”

You damn near hit your head on the hood. Having been so engrossed in checking every square inch of the engine block, you didn’t notice anyone pull off the side of the road. You pried yourself away from Baby and took in the stranger’s appearance. 

He stood before you in boot-cut jeans, a faded T-shirt, a dull-looking flannel, and a worn leather jacket. Only God knows how he was putting up with the summer heat in that get-up. 

You were bordering on overheating in the simple, all-black tank top and jeans outfit you were sporting. The only upside to your look was that it hid grease a lot better than the floral sundress you were originally going to wear today. The stranger had his thumbs hooked in the pockets of his jeans, adding to the overall cockiness that graced his features. 

“And most people introduce themselves before jumping right into aesthetic criticism.”

He smirked - almost drunkenly - and shot out a hand. “Name’s Dean.” Tentatively, you shook his hand, realizing as his hand seemed to swallow yours just how large this man was, and how there was no one in sight for miles.

“My name is Y/N, and uh, it looks like I’m in need of a new spark plug. Do you happen to know where the closest auto parts store is?” 

“Oh that’s about 10 miles that way.” He jabbed a thumb down the dusty old highway towards the town you were headed to and dramatically dropped his hand back to his side. “I can give you a ride if you’d like. Gonna have to make a pit stop at the bar first.”

“That’s alright. I should probably let the engine cool a bit more before I fix her up.” Dean nodded knowingly and jerked his head to the side, gesturing to his car- which was black. That explained his opening line some.

“Hop in, and don’t mind the backseat driver.” That sinking feeling of vulnerability hit you again when he said this, not sure if this was such a good idea anymore.

“Ehhhhh, thanks but I think I’m just gonna call a cab,” you tried hiding your discomfort and easing the tension with a chuckle, but there’s no way he didn’t notice you taking a step back. 

“Nonsense! Crowley ‘n I are more than willing to take you into town. No strings attached. Promise.” 

You were about to respond but were cut off when a gruff British voice came from the black beauty of a car’s backseat. “Squirrel! Get on with it, will ya?! I’ve got that meeting.”

Dean grinned wide and gestured to his car “C’mon now sweetheart, don’t want to make him late do you?” 

Despite your reservations, you nodded and headed to the passenger seat. Something about the glint in his eye told promises of a good time, which you honestly needed quite desperately. And how could anyone with the nickname ‘Squirrel’ be dangerous? 

Buckling in, the same voice from before greeted you, this time accompanied by an older, nonetheless handsome, face, and a much smoother tone. “Hello darling, don’t believe we’ve met before.” He stuck his hand out between the seats, looking for a handshake. “M’name’s Crowley, and you are?” 

“My name’s-“

“Her name’s Y/N! And she’s coming with us to the bar!” You jumped a little, startled by Dean’s abrupt addition. 

“Yeah…. What he said” You provide your hand for Crowley to shake but he instead took it gently and kissed the back of it. “Enchanté, darling. May I be so bold as to say you are absolutely ravishing?” 

The bubbling laughter that came from you couldn’t seem to be stopped. “Thank you, really, you’re too kind.” 

With that, Dean took off.

———————————————————

It was your third beer of the night. You normally didn’t like to drink too much, but with such a charming man as Crowley paying, and Dean crowing a wretched rendition of some 80’s hair metal song you vaguely knew the tune of, it seemed like a good idea. Crowley was quite the conversationalist, somehow charming enough to relax you and get you talking. It must’ve been the accent.

“So what’re you and Dean doing driving around together to this tumbleweed town?”

“Just doin’ what besties do. Driving ‘cross country, Love.” He seemed to enjoy lavishing you in cheesy pet names. 

“S’he your chauffeur of something? Like why were you in the back seat?” 

“Not a chauffeur, kiddo.” A large hand slapped onto your shoulder, and you again jumped, turning to see Dean had wrapped his arm around you and plopped onto the empty barstool beside you. “And not your bestie, Crowley.” 

“Squirrel,” He dramatically clutched at his chest, and braced himself on the bar, “you wound me!” 

A not-too-entirely sober giggle bubbles out from behind your lips. ”How’d s’meone as big ‘n rough around the edges get that nickname, Dean-o?” You ruffled his short, yet poofy hair; you were just tipsy enough to not notice him tense at the affection.

“Well our little Dean here has a taller broth-“

“Don’t.” This time, you did notice Dean’s tension. 

“Aw come on now Dean, our little pet’s just tryin-“

He slammed his hands on the bar, a scar peeking out from under the rolled sleeve of his flannel seeming to glow red. “I said,” His eyes flashed to a solid black and you drew a sharp breath in, sobering up, “don’t.” 

You tried backing away, tripping over the barstool, and stumbling back before a large, calloused hand snatched your arm. “I’m just, uh, I’m gonna go now... get those spark plugs so if you could just, uh, let go, I’ll be fine.” Your heart was racing, your pulse pounding in your ears. Demons. You hitched a ride with demons. 

“Now, now sweetheart,” Crowley’s voice came from behind you, breath brushing against your ear. You were so fixated on Dean, you hadn’t noticed him moving. “we were just getting started with you.”


	2. The Joker

“Now now sweetheart, we were just getting started with you,” Dean seemed to snap out of it at Crowley’s muttering, remembering they were in public surrounded by humans.

“Yeah, Y/N, you haven’t even sung karaoke yet.” Your blood was still pounding in your ears, but you nodded. The best way to get out of this alive was to play along. Dean’s face twisted into a half-scowl, half-pout as though he heard your thoughts. 

“I’m always a sucker for 70s hits,” you managed to pant out. Dean lit up at that, sashaying off to get the attention of the waitress running the karaoke set up. 

“Well done there, Y/N. Never seen anyone handle him that well.” You turned and faced the demon behind you. 

“Excuse me?” The adrenaline was wearing off now, but you were still on high-alert. 

“With Dean, usually galls get a little concerned by his other eye color. But you- you kept your cool. That and the drab attire, and the sad excuse for a set of wheels. I’m going to reach here and say maybe, just maybe, you’re a hunter?” 

“I have no idea what you’re talking about.” 

He chuckled at that. “Of course not. Now go and caterwaul with our boy up on that sorry stage, pet. This night might just go your way if you keep playing along.” 

You nodded. “I’ll need another drink first.” 

“Of course, of course.” He motioned to the bartender and bought you a shot of whiskey. It was risky getting drunk around demons but you needed all the courage you could get, liquid or otherwise. Gulping down the amber drink, you took a deep, steadying your breath, and made your way up next to Dean. 

“I hope you like the Steve Miller Band.” His eyebrows bounced as he handed you your own mic. The short drum intro filled the dingy tavern and the lyrics to one of your favorite songs popped on the screen in front of you and Dean. 

“Some call me a space cowboy yeah,  
Some call me the gangster of love.  
Some people call me Maurice” 

He pulled the mic away to imitate the dramatic twang of the guitar strings.

“'Cause I speak of the pompitous of love” 

He turned to you, continuing his crooning, pointing at you as if singing the next verse directly for you. 

“People talk about me baby  
Say I'm doin' you wrong, doin' you wrong  
Well don't you worry baby, don't worry” 

Dean sauntered closer, his husky voice doing things to you that it definitely shouldn’t.

“'Cause I'm right here at home.” 

He leaned into you so your chests were pressed against one another and his lips brushed against your ear. “Your turn now.”

He pulled away too quickly for your liking and you had to clear your throat. You heard Dean chuckle when you shook your head, trying to clear the dirty thoughts that had crept in. Letting the whiskey guide you, you started moving to the beat, hips, and shoulders swaying the best they could before staring directly into Dean’s luscious green eyes and giving the song your best.

“'Cause I'm a picker  
I'm a grinner   
I'm a lover” 

You ran a finger down Dean’s chest, barely noticing the hooping and hollering it got you from the crowd.

“And I'm a sinner” 

You spun around, continuing your movements against Dean. His lips grazed your neck.

“Playin' my music in the sun  
I'm a joker  
I'm a smoker  
I'm a mid-night toker”

Dean leaned further into you so his lust-laced voice could be heard in the microphone, singing the next part in tandem with you, 

“I get my lovin' on the run   
Ooh, ooh, ooh, ooh”

—————————————————————-

The rest of the song seemed to blur, you and Dean making the perfect couple. Your performance together was nothing short of sultry. When the last notes played, the other patrons of the bar gave a standing ovation. You giggled, your cheeks flushed, having forgotten the dangerous edge to the situation and having a genuinely good time. Dean couldn’t stop grinning at you, his eyes never leaving you as you both climbed down off the stage. 

“Well done you two, well done.” Crowley cheered. “You lovebirds keep having fun, I have some business to tend to.” 

“And what exactly is that business, Crowley?” You asked pointedly, jaw flexing with your efforts to keep a stern look on your face. He smirked before looking over your shoulder at Dean, who had his arms wrapped around you and chin resting atop your head. Dean sat down in the booth across from Crowley, pulling you into his lap. 

“Well, Crowls? Not nice to leave a lady hanging.” You felt him tilt his head above you and you smirked, puffing out your chest with the satisfaction of having him back you up.

“Well darling, since you so… kindly asked. The job of the King of Hell is never-ending, as is his business.” 

You instantly deflated. “Shiiiiit.” You whispered.

“Come on now, Y/N. You knew what you were getting into. And we’re not so bad are we?” Dean brushed your hair away from your neck to clear a spot for his lips to trail along. You sighed and rolled your head back against his shoulder so your eyes could meet. 

“Demons killed my parents.”

“So? They killed mine too.” 

You scoffed and shifted out of his lap. “Demons don’t have parents, Dean.”

Crowley piped up. “And he’s not a demon, love.” 

You narrowed your eyes and drunkenly whipped your head in his direction. “I saw his eyes do the thing, only demons do that.” Dean chuckled and took a swig of a half-empty beer someone else had left on the table. You grimaced.

“You’re right sweetcheeks, but so’s Crowley. Not a demon. Just cursed.” He rolled up his sleeve further to reveal the entirety of his strange scar. “See? Cursed.”

“Then what’re you doing hanging out with him,” you poked your thumb in Crowley’s direction, making him roll his eyes and lean back into the bench. “the ‘King of Hell’.” A throaty laugh rumbled in Dean’s chest at your air quotes and poor attempt at Crowley’s accent.

“Just having some fun, blowing off steam. But come on, you can’t tell me you haven’t heard of me before if you’re a hunter.”

“You never gave me a last name dumbass, and there’s thousands of Dean’s in the world.”

“Winchester dear. His last name is Winchester.” Crowley’s voice dripped with disgust. The wheels turned in your head until two and two finally clicked. Your jaw slacked, your eyes widened and you looked back at Dean. “Bingo. You’re sat next to Dean Winchester darling.”

“A-apocalypse Dean Winchester? Sam and Dean Dean Winchester?” Dean scowled at that but you kept going. “John Winchester’s kid? Bobby’s kid?!” 

“You knew Bobby?” 

You slid out of the booth wobbling a bit. “Of course I knew Bobby, the man practically raised me! Took me in after the demon-after my parents-” 

“Of course he did, he was always taking in strays.”

“Strays? Oh, go to hell Dean.” 

He tipped the beer bottle in your direction before finishing it off in one swallow. “Been there, rather not go back. Full offense.” Crowley nodded, not even looking perturbed.

“Fuck you, I’m getting out of here.” 

Dean scoffed. “You’re in no condition to fix your truck, Y/N.” 

“That means a lot coming from him.” You glared at Crowley.

“Fine, but I am not spending the night with the likes of you two.” They both laughed as you waved your finger between them, your other hand perched on your hip. 

“Fine by me doll, but at least do me a solid and go another round on the karaoke machine.” You tittered, still very much affected by your previous drinks. 

“Okay! I choose the song thoooooough.” You sang out, ambling toward the stage once again. With your back turned to them, you completely missed the wordless conversation shared by the cohorts. 

Crowley’s eyes were full of insinuation before Dean narrowed his and responded curtly. “Back off, Crowls. I’m not gonna do anything stupid.”

“Said the same thing when you went into that gas station.” 

Dean pushed himself out of the booth. “Shut your pie hole and let me live.”


End file.
